CA2137221C - Preparation of 3,4,4-trisubstituted piperidinyl-n-alkylcarboxylates and intermediates - Google Patents

Preparation of 3,4,4-trisubstituted piperidinyl-n-alkylcarboxylates and intermediates Download PDF

Info

Publication number
CA2137221C
CA2137221C CA2137221A CA2137221A CA2137221C CA 2137221 C CA2137221 C CA 2137221C CA 2137221 A CA2137221 A CA 2137221A CA 2137221 A CA2137221 A CA 2137221A CA 2137221 C CA2137221 C CA 2137221C
Authority
CA
Canada
Prior art keywords
compound
alkyl
crystalline
salt
compounds
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Fee Related
Application number
CA2137221A
Other languages
English (en)
French (fr)
Other versions
CA2137221A1 (en
Inventor
Scott A. Frank
Douglas E. Prather
Jeffrey A. Ward
John A. Werner
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Eli Lilly and Co
Original Assignee
Eli Lilly and Co
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Eli Lilly and Co filed Critical Eli Lilly and Co
Publication of CA2137221A1 publication Critical patent/CA2137221A1/en
Application granted granted Critical
Publication of CA2137221C publication Critical patent/CA2137221C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D211/00Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/08Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
    • C07D211/10Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms
    • C07D211/14Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms with hydrocarbon or substituted hydrocarbon radicals attached to the ring nitrogen atom
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D211/00Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/08Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
    • C07D211/18Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D211/34Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00Drugs for disorders of the alimentary tract or the digestive system
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/06Anti-spasmodics, e.g. drugs for colics, esophagic dyskinesia
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D211/00Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/08Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
    • C07D211/18Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D211/20Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms
    • C07D211/22Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms by oxygen atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Engineering & Computer Science (AREA)
  • Animal Behavior & Ethology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Hydrogenated Pyridines (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
CA2137221A 1993-12-08 1994-12-02 Preparation of 3,4,4-trisubstituted piperidinyl-n-alkylcarboxylates and intermediates Expired - Fee Related CA2137221C (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US08/164,074 US5434171A (en) 1993-12-08 1993-12-08 Preparation of 3,4,4-trisubstituted-piperidinyl-N-alkylcarboxylates and intermediates
US08/164,074 1993-12-08

Publications (2)

Publication Number Publication Date
CA2137221A1 CA2137221A1 (en) 1995-06-09
CA2137221C true CA2137221C (en) 2011-02-22

Family

ID=22592858

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2137221A Expired - Fee Related CA2137221C (en) 1993-12-08 1994-12-02 Preparation of 3,4,4-trisubstituted piperidinyl-n-alkylcarboxylates and intermediates

Country Status (30)

Country Link
US (1) US5434171A (OSRAM)
EP (3) EP0984004A3 (OSRAM)
JP (2) JP3834075B2 (OSRAM)
KR (1) KR100356239B1 (OSRAM)
CN (2) CN1057294C (OSRAM)
AT (1) ATE200279T1 (OSRAM)
AU (1) AU681198B2 (OSRAM)
BR (1) BR9404842A (OSRAM)
CA (1) CA2137221C (OSRAM)
CO (1) CO4290427A1 (OSRAM)
CZ (1) CZ290559B6 (OSRAM)
DE (1) DE69427017T2 (OSRAM)
DK (1) DK0657428T3 (OSRAM)
ES (1) ES2155844T3 (OSRAM)
FI (2) FI106455B (OSRAM)
GR (1) GR3036136T3 (OSRAM)
HU (1) HUT71489A (OSRAM)
IL (1) IL111843A (OSRAM)
MY (1) MY121543A (OSRAM)
NO (1) NO302884B1 (OSRAM)
NZ (1) NZ270039A (OSRAM)
PE (1) PE41495A1 (OSRAM)
PL (1) PL181734B1 (OSRAM)
PT (1) PT657428E (OSRAM)
RU (1) RU2145958C1 (OSRAM)
SI (1) SI0657428T1 (OSRAM)
TW (1) TW290540B (OSRAM)
UA (1) UA52577C2 (OSRAM)
YU (2) YU49312B (OSRAM)
ZA (1) ZA949584B (OSRAM)

Families Citing this family (64)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2722497B1 (fr) * 1994-07-13 1996-08-14 Synthelabo Esters de alpha-4-chlorophenyl)-4-(4-fluorophenyl)methyl) piperidine-1-ethanol, leur preparation et leur application en therapeutique
HN1999000149A (es) 1998-09-09 2000-01-12 Pfizer Prod Inc Derivados de 4,4-biarilpiperidina
GB9912413D0 (en) 1999-05-28 1999-07-28 Pfizer Ltd Compounds useful in therapy
GB9912411D0 (en) 1999-05-28 1999-07-28 Pfizer Ltd Compounds useful in therapy
GB9912417D0 (en) 1999-05-28 1999-07-28 Pfizer Ltd Compounds useful in therapy
GB9912415D0 (en) 1999-05-28 1999-07-28 Pfizer Ltd Compounds useful in therapy
GB9912410D0 (en) 1999-05-28 1999-07-28 Pfizer Ltd Compounds useful in therapy
GB9912416D0 (en) 1999-05-28 1999-07-28 Pfizer Ltd Compounds useful in therapy
US6451806B2 (en) 1999-09-29 2002-09-17 Adolor Corporation Methods and compositions involving opioids and antagonists thereof
US6469030B2 (en) 1999-11-29 2002-10-22 Adolor Corporation Methods for the treatment and prevention of ileus
EP1404323B1 (en) * 2001-06-05 2009-10-28 The University of Chicago Use of methylnaltrexone to treat immune suppression
US20030068829A1 (en) * 2001-06-25 2003-04-10 Symyx Technologies, Inc. High throughput crystallographic screening of materials
SI2939696T1 (sl) 2001-10-18 2016-06-30 Nektar Therapeutics Polimerni konjugati opioidnih antagonistov
US6794510B2 (en) * 2002-08-08 2004-09-21 Adolor Corporation Processes for the preparation of peripheral opioid antagonist compounds and intermediates thereto
US7381721B2 (en) * 2003-03-17 2008-06-03 Adolor Corporation Substituted piperidine compounds
PT2368553E (pt) 2003-04-08 2015-03-03 Progenics Pharm Inc Formulações farmacêuticas contendo metilnaltrexona
JP2006522817A (ja) * 2003-04-08 2006-10-05 プロジェニックス ファーマシューティカルズ,インコーポレーテッド 過敏性腸症候群を処置するための末梢オピオイドアンタゴニスト、特にメチルナルトレキソンの使用
US6992090B2 (en) 2003-06-16 2006-01-31 Adolor Corporation Substituted piperidine compounds and methods of their use
FR2861304B1 (fr) * 2003-10-23 2008-07-18 Univ Grenoble 1 Modulateurs des canaux cftr
US20050148630A1 (en) * 2003-12-02 2005-07-07 Carpenter Randall L. Methods of preventing and treating non-opioid induced gastrointestinal dysfunction
US8946262B2 (en) * 2003-12-04 2015-02-03 Adolor Corporation Methods of preventing and treating gastrointestinal dysfunction
ES2445585T3 (es) * 2003-12-16 2014-03-04 Nektar Therapeutics Composiciones monodispersas de naloxol PEGilado
US20060182692A1 (en) 2003-12-16 2006-08-17 Fishburn C S Chemically modified small molecules
US7087749B2 (en) * 2004-03-11 2006-08-08 Adolor Corporation Substituted piperidine compounds and methods of their use
US20050240177A1 (en) * 2004-04-26 2005-10-27 Packaging Service Corporation Of Kentucky Electrosurgical forceps
US7700626B2 (en) 2004-06-04 2010-04-20 Adolor Corporation Compositions containing opioid antagonists
US8039456B2 (en) 2004-08-12 2011-10-18 Helsinn Therapeutics (U.S.), Inc. Method of stimulating the motility of the gastrointestinal system using ipamorelin
PT1789067E (pt) * 2004-08-12 2012-08-06 Helsinn Healthcare Sa Utilização de hormona do crescimento secretagogo para a estimulação da motilidade do sistema gastrointestinal
US20060063792A1 (en) * 2004-09-17 2006-03-23 Adolor Corporation Substituted morphinans and methods of their use
US20060211733A1 (en) * 2005-03-04 2006-09-21 Adolor Corporation Methods of preventing and treating opioid bowel dysfunction
US8518962B2 (en) 2005-03-07 2013-08-27 The University Of Chicago Use of opioid antagonists
US8524731B2 (en) 2005-03-07 2013-09-03 The University Of Chicago Use of opioid antagonists to attenuate endothelial cell proliferation and migration
US9662325B2 (en) 2005-03-07 2017-05-30 The University Of Chicago Use of opioid antagonists to attenuate endothelial cell proliferation and migration
US9662390B2 (en) * 2005-03-07 2017-05-30 The University Of Chicago Use of opioid antagonists to attenuate endothelial cell proliferation and migration
AR057325A1 (es) 2005-05-25 2007-11-28 Progenics Pharm Inc Sintesis de (s)-n-metilnaltrexona, composiciones farmaceuticas y usos
AR057035A1 (es) 2005-05-25 2007-11-14 Progenics Pharm Inc SíNTESIS DE (R)-N-METILNALTREXONA, COMPOSICIONES FARMACÉUTICAS Y USOS
US7956220B2 (en) * 2005-07-01 2011-06-07 Jenrin Discovery MAO-B inhibitors useful for treating obesity
US7914776B2 (en) * 2005-10-07 2011-03-29 Adolor Corporation Solid dispersions of opioid antagonists
US20070092576A1 (en) * 2005-10-20 2007-04-26 Adolor Corporation Compositions containing opioid antagonists
US7538110B2 (en) 2005-10-27 2009-05-26 Adolor Corporation Opioid antagonists
CN100383121C (zh) * 2006-03-07 2008-04-23 天津泰普药品科技发展有限公司 阿韦苄酯化合物及其制备方法和以该化合物制备阿韦莫哌的工艺
CN101426481B (zh) 2006-04-21 2012-12-05 帝斯曼知识产权资产管理有限公司 阿片受体拮抗剂的用途
TWI489984B (zh) 2006-08-04 2015-07-01 Wyeth Corp 用於非經腸道傳輸化合物之配方及其用途
BRPI0719305A2 (pt) * 2006-11-22 2014-02-04 Progenics Pharm Inc (r)-n-estereoisômeros de análogos de 7,8-saturados-4,5-epóxi-morfinano
MX351611B (es) 2007-03-29 2017-10-20 Wyeth Llc Formas de cristal de bromuro de (r)-n-metilnaltrexona y uso de las mismas.
MX2009010552A (es) 2007-03-29 2009-12-14 Progenics Pharm Inc Antagonistas de receptor de opioide periferico y usos de los mismos.
HUE025662T2 (en) 2007-03-29 2016-04-28 Wyeth Llc Peripheral opioid receptor and antagonists and their uses
US8471022B2 (en) 2008-02-06 2013-06-25 Progenics Pharmaceuticals, Inc. Preparation and use of (R),(R)-2,2′-bis-methylnaltrexone
AU2009225434B2 (en) 2008-03-21 2014-05-22 The University Of Chicago Treatment with opioid antagonists and mTOR inhibitors
EP2331140B1 (en) 2008-08-11 2018-07-04 Nektar Therapeutics Multi-arm polymeric alkanoate conjugates
CA2676881C (en) 2008-09-30 2017-04-25 Wyeth Peripheral opioid receptor antagonists and uses thereof
CN101429154B (zh) * 2008-11-14 2011-01-05 天津泰普药品科技发展有限公司 无水阿维莫泮及其药物组合物
US20100311782A1 (en) 2009-06-08 2010-12-09 Adolor Corporation Substituted piperidinylpropanoic acid compounds and methods of their use
EP3569234A1 (en) 2009-12-04 2019-11-20 Alkermes Pharma Ireland Limited Morphinan derivatives for the treatment of drug overdose
WO2011161646A2 (en) 2010-06-25 2011-12-29 Ranbaxy Laboratories Limited Process for the preparation of alvimopan or its pharmaceutically acceptable salt or solvate thereof
WO2012088422A1 (en) 2010-12-22 2012-06-28 Nektar Therapeutics Multi-arm polymeric prodrug conjugates of taxane-based compounds
WO2012088445A1 (en) 2010-12-22 2012-06-28 Nektar Therapeutics Multi-arm polymeric prodrug conjugates of cabazitaxel-based compounds
WO2012166555A1 (en) 2011-05-27 2012-12-06 Nektar Therapeutics Water - soluble polymer - linked binding moiety and drug compounds
CN103360302B (zh) * 2012-03-29 2015-08-26 北大方正集团有限公司 阿维莫泮的纯化方法
US10314839B2 (en) 2014-10-20 2019-06-11 Elysium Therapeutics, Inc. Diversion-resistant opioid formulations
WO2017059459A1 (en) 2015-10-01 2017-04-06 Elysium Therapeutics, Inc. Polysubunit opioid prodrugs resistant to overdose and abuse
US10335406B2 (en) 2015-10-01 2019-07-02 Elysium Therapeutics, Inc. Opioid compositions resistant to overdose and abuse
WO2018170465A1 (en) 2017-03-17 2018-09-20 Elysium Therapeutics, Inc. Polysubunit opioid prodrugs resistant to overdose and abuse
CN119816485A (zh) * 2022-10-27 2025-04-11 株式会社京都创药研究所 萘衍生物的晶体

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4891379A (en) * 1987-04-16 1990-01-02 Kabushiki Kaisha Kobe Seikosho Piperidine opioid antagonists
US5136040A (en) * 1991-02-26 1992-08-04 Eli Lilly And Company Preparation of substituted tetrahydropyridines
US5250542A (en) * 1991-03-29 1993-10-05 Eli Lilly And Company Peripherally selective piperidine carboxylate opioid antagonists
US5159081A (en) * 1991-03-29 1992-10-27 Eli Lilly And Company Intermediates of peripherally selective n-carbonyl-3,4,4-trisubstituted piperidine opioid antagonists
ZA922180B (en) * 1991-03-29 1993-09-27 Lilly Co Eli Piperidine derivatives

Also Published As

Publication number Publication date
RU2145958C1 (ru) 2000-02-27
FI106860B (fi) 2001-04-30
HU9403466D0 (en) 1995-02-28
HUT71489A (en) 1995-11-28
CN1057294C (zh) 2000-10-11
EP1607387A2 (en) 2005-12-21
CA2137221A1 (en) 1995-06-09
JPH07215937A (ja) 1995-08-15
YU49312B (sh) 2005-06-10
YU82304A (sh) 2006-03-03
IL111843A (en) 2000-02-29
YU70294A (sh) 1997-07-31
JP2006070042A (ja) 2006-03-16
HK1013826A1 (en) 1999-09-10
RU94042903A (ru) 1996-10-27
NO944644D0 (no) 1994-12-02
US5434171A (en) 1995-07-18
NO944644L (no) 1995-06-09
EP0657428A1 (en) 1995-06-14
MY121543A (en) 2006-02-28
FI106455B (fi) 2001-02-15
PL181734B1 (pl) 2001-09-28
KR950017957A (ko) 1995-07-22
TW290540B (OSRAM) 1996-11-11
IL111843A0 (en) 1995-03-15
ES2155844T3 (es) 2001-06-01
FI20000353L (fi) 2000-02-17
KR100356239B1 (ko) 2002-12-26
ATE200279T1 (de) 2001-04-15
AU7917094A (en) 1995-06-15
CN1223257A (zh) 1999-07-21
UA52577C2 (uk) 2003-01-15
DK0657428T3 (da) 2001-05-07
NO302884B1 (no) 1998-05-04
PE41495A1 (es) 1995-11-28
ZA949584B (en) 1996-06-03
BR9404842A (pt) 1995-08-08
NZ270039A (en) 1996-08-27
EP0984004A2 (en) 2000-03-08
PL306068A1 (en) 1995-06-12
PT657428E (pt) 2001-07-31
EP0984004A3 (en) 2003-10-15
CZ299294A3 (en) 1995-10-18
FI945703A0 (fi) 1994-12-02
JP3834075B2 (ja) 2006-10-18
CZ290559B6 (cs) 2002-08-14
EP1607387A3 (en) 2007-01-03
GR3036136T3 (en) 2001-09-28
DE69427017D1 (de) 2001-05-10
CN1111239A (zh) 1995-11-08
CO4290427A1 (es) 1996-04-17
AU681198B2 (en) 1997-08-21
CN1121387C (zh) 2003-09-17
SI0657428T1 (en) 2001-08-31
EP0657428B1 (en) 2001-04-04
FI945703L (fi) 1995-06-09
DE69427017T2 (de) 2001-09-06

Similar Documents

Publication Publication Date Title
CA2137221C (en) Preparation of 3,4,4-trisubstituted piperidinyl-n-alkylcarboxylates and intermediates
US5250542A (en) Peripherally selective piperidine carboxylate opioid antagonists
US5270328A (en) Peripherally selective piperidine opioid antagonists
JP3022951B2 (ja) アロイル−ピペリジン誘導体
KR100229117B1 (ko) 피페리딘 유도체
CZ283508B6 (cs) Deriváty N-acyl-alfa-aminokyselin, způsob jejich výroby a farmaceutické přípravky na jejich bázi
JPH10101565A (ja) 胃腸血行障害を治療および予防するための医薬製剤を製造するためのベンズアゼピン−n−酢酸誘導体の使用
OA11908A (en) Crystalline forms of eto2c-ch2-(r)cgl-aze-pab-oh.
CA2064373C (en) Piperidine derivatives
ES2354968T3 (es) Derivados de piperidina antihistamínicos e intermedios para la preparación de los mismos.
JP2650739B2 (ja) 分割化アミノピロリジン神経防護剤
HK1027558A (en) Trisubstituted-piperidinyl-n-alkylcarboxylates as opioid antagonists
HK1084950A (en) 3,4,4-trisubstituted piperidine derivatives and their use as opioid antagonists
HK1013826B (en) Preparation of 3,4,4-trisubstitutedpiperidinyl-n-alkylcarboxylates and intermediates, useful as opioid antagonists
JP2001524466A (ja) ニューロキニンアンタゴニストとしての置換されたオキシム
CA3125655A1 (en) Crystalline forms of (s)-2-(7-cyano-1h-benzimidazol-1 yl)- n-{1-[4-(1-cyano-1-methylethyl)phenyl]ethyl}acetamide

Legal Events

Date Code Title Description
EEER Examination request
MKLA Lapsed

Effective date: 20141202